I remember it was bright and sunny that day in Chicago. I remember the sound of the elevated train rattling over the roof of the jewelry store. I remember her looking at a ring in the glass display case, pointing, and then the lady behind the counter removing the ring and putting it on top of the case and standing slightly back from it just so—a routine that itself has become part of the engagement ritual. I remember Lori’s face when the lady asked her if she liked the ring. The expression in Lori’s eyes—yes, she liked it, very much.

The thing was, I was as broke as I was in love.

By then, toward the end of 1994, Lori and I had been, as my mother would put it, “living in sin” for two years; we’d been dating for three. I was 23. She was 24. That we would marry had been decided long before that day in the jeweler, at least in my mind. That had been determined when we moved into a small Chicago apartment a few blocks from Wrigley Field. Lori was working her first job after college and I’d been accepted into graduate school at Northwestern. “Well,” she’d said, “There’s no point in you living on campus. You’ll move in with me.” I will? I thought.

She kept talking: “There’s no point in two rents. We can’t afford that.” Wait, ‘we’ can’t afford that. We? I don’t remember exactly what I said in response to these profound, declarative pronouncements she made with such ease, but I remember clearly not wanting to show a flinch. I remember that what I did say amounted to me buying time with something along the lines of, “That sounds like it makes sense.”

I spent almost every second of the months following that conversation considering how I’d gotten there: How I had pursued her despite that night she “mistakenly” stood me up. How, after quitting the football team my sophomore year of college, I’d taken a work-study job in the locker room washing the jocks of my former teammates; how I did it with a smile because it meant that while the jocks tumbled in the industrial dryers, I could slip out and sidle up next to her on the field where she was doing her own work-study job, as the student assistant to the team’s athletic trainer.

There was that night, the night, on the porch swing of a big, old clapboard college house, tipsy on sangría, when, at last, we kissed. There was another night, at our college bar, when she turned my way, looked across the room, through everyone else, at me—at me. Man, those eyes. I had to lean back against the bar. The word Wow popped like a bubble-gum bubble in my head. “Desperado” was on the jukebox. Her favorite song. Don Henley going on about “it may be rainin’ but there’s a rainbow above you.” She smiled my way and it lifted me out of where’d I’d been—lost, hopeless, already so cynical—and carried me to … well, to her smile, to her loving optimism. So, yes, of course, when I arrived Chicago with my two suitcases I moved into her apartment, suddenly our apartment—in my mind, forever. Maybe she was right: Maybe we couldn’t have afforded the two rents. But I knew I could not afford to risk losing her.

And we couldn’t—no, I couldn’t—afford that ring. Not now. I was a journalism graduate student who worked part-time as a bartender on an architectural tour boat on the Chicago River. We weren’t supposed to be ring shopping that day. That hadn’t been the plan. We were just out. Next thing you know we found ourselves in the Diamond District. Then we were in one jeweler, then another. Then Lori pointed, and the lady behind the counter did her thing.

Lori put the ring on. She didn’t look at me, because she knew I couldn’t afford it and she didn’t want to make me feel bad. Still, I could see whatever those emotions were that were making her eyes seem even bigger and browner. Three-quarters of a carat looked like a goddamn doorknob. While it was on her finger, when the lady behind the counter looked at me and tilted her head as if to say, awwww, I remember that I had a kind of an out-of-body experience. I watched myself say: “We’ll take it.”

“Really?” the lady behind the counter said.

“Really?” Lori said.

“Yes, really,” I said.

It was pure happenstance. Only it wasn’t. A few days earlier I’d been at the student loan office on campus. Because we’d been smart with Lori’s salary and my student loan money—really, because Lori had been smart with her salary and my student loan money—my tuition was caught up. The woman at the office reminded me all was current, but added that I could take out a bit more cash if I needed any for living expenses. It was already there, she said, if I wanted it. So I’d taken it. Just in case.

The ring had to be fitted. We were told it would take half an hour. Next door was a diner. We had breakfast while we waited. I remember holding hands across the table, around the plates of eggs and hash browns. We picked up the ring. The lady looked at Lori and asked if she was going to wear it home. No, I said, before Lori had a chance to answer. After all, we weren’t dealing with a pair of shoes here. I said I had not yet proposed The Question. I asked that the ring be placed in one of those little felt boxes. We rode on the rattling “el” train back to Wrigleyville, bought the first bottle of champagne I would ever drink, and returned to her apartment—our apartment.

Lori sat in the oversized red chair with the lame, allegedly Native American pattern. I got down on my knee and I asked her if she would marry me. Despite everything we’d done on that bright, sunny day, despite all of our little life together up to that moment, I swear her answer stunned me. Almost 20 years later, it still stuns me. I can hardly believe it. She said “Yes.”

Bonus: You might just meet The One at our Single in the City party tomorrow night. Check out our Top Singles before you go.

—Image courtesy of Shutterstock

Follow editor-at-large Maximillian Potter on Twitter at @maxapotter.